Judging by the flaking white paint, broken, grimy windows, thigh-high grass and faded sign, it would seem there is more history to Hillsborough’s Colonial Inn than there is future.

Two signs adorn the 175-year-old inn’s façade. One denotes the building, a former burnished dining and lodging destination on West King Street, a “best of” winner for online guide Citysearch. The other proclaims, by order of Hillsborough Town Hall, the decaying inn condemned.

“Right now, it’s in a pretty sad state,” says Hillsborough Mayor Tom Stevens.

It’s in such a state that owner Francis Henry asked the Hillsborough Historic District Commission for permission to raze the building. His request was denied.

Local ordinances prohibit the demolition of historically significant structures without the commission’s approval. And, as Anna Currie, vice chairwoman of the commission, pointed out, there is no building in Hillsborough with as much historical significance.

Built in 1838, the two-story inn was a centrally located hotel that later morphed into a popular restaurant and event space. Stevens, like many in Hillsborough, remembers Sunday lunches at the restaurant with the inn’s popular fried chicken and family-style vegetable dishes.

“It was a symbol of Hillsborough,” Stevens says. “It’s a real landmark for the town.”

Currie noted that the building is the only one in Orange County to be recognized by the state as a place of historical significance. “It’s near and dear to people’s hearts,” she said. “The town would like nothing better than for someone to bring it back to significance.”

Now that seems a possibility. A number of individuals have offered to pay for the restoration of the building. Citing the sensitive nature of real estate dealings, Stevens declined to identify them.

But the mayor also says others have pitched holding fundraising campaigns with Kickstarter, an online crowdfunding platform. Given the interest, Stevens says he’s “optimistic” that the inn will eventually be restored.

“It will continue to be a part of Hillsborough’s streetscape,” he said. “We just have to let the process play out.”

Dozens of locals rallied at last week’s commission hearing, describing Henry as a businessman with little interest in preserving the town’s historic character.

“Mr. Henry seems to have no love for historic structures or nostalgic places. He has blood on his hands,” wrote Chip Millard, a Chatham County photographer who organized opposition to the inn’s demolition on a blog launched to save the inn.

Henry, who declined to talk with INDY Week about the inn, has a complicated history in Orange County. A UNC-Chapel Hill graduate, he was a popular soccer player in the late 1960s. The university’s plush field hockey and lacrosse stadium is named for him.

But his business dealings have rankled some residents, including people in Chapel Hill who complained in early 2008 when the Ram’s Head Rathskeller, a beloved, underground restaurant owned by Henry on Franklin Street, was shuttered. Its contents were later auctioned off to pay back taxes.

Henry has also had a tortured history in Hillsborough since purchasing the Colonial Inn in a foreclosure auction in 2002. In 2004, the town sued Henry and began fining him for demolition by neglect at the property. The town and Henry reached a settlement in June 2005, with Henry agreeing to pay the town $2,500 for preservation.

In September 2007, Henry filed a request to rezone the property for commercial uses, but he withdrew it in early 2008 after neighbors complained. A second lawsuit from the town followed in June 2010, with the court later ordering Henry to make repairs at the property.

The inn has languished until Henry filed a request to demolish the inn in June. At last week’s meeting, Henry described it as a symbolic request to express his property rights.

Still, Henry told town officials at last week’s meeting that he had several options for the inn.

“We’d like to see something happen,” Stevens says. “Whether that’s by the current owner or someone else, the important thing is that it remains.”

This article appeared in print with the headline “Through the past, darkly”